1. Field of the Invention
This invention relates to novel phosphoroamidothioate and phosphoroamidodithioate compounds, to compositions thereof which are useful as pesticides, for example, as arthropodicides (that is, insecticides and acaricides), nematocides, and fungicides, and to a method of controlling pests, such as insects, acarids, nematodes, and fungi. The compounds are effective when applied by soil application techniques and by foliar application techniques.
2. Description of the Prior Art
Ollinger, U.S. Pat. No. 4,263,288, issued Apr. 21, 1981, discloses acaricidal, insecticidal, and nematocidal phosphoroamidothioates having the formula EQU [(A--N.dbd.C(R)](N(R.sup.1)]P(.dbd.X)(R.sup.2)(SR.sup.3)
wherein
A is aryl, PA1 R is hydrogen or alkyl, PA1 R.sup.1 is alkyl, cycloalkyl, alkenyl, alkynyl or aralkyl, PA1 R.sup.2 is alkylthio, aryloxy, or amino, PA1 R.sup.3 is alkyl, and PA1 X is O or S. PA1 R.sup.1 and R.sup.2 are alkyl, alkenyl, diaryl, alkaryl, or aralkyl groups; PA1 X and X.sup.1 are O, S, or Se; and PA1 n is an integer from 2-9. PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms or, when X and Y are both S, CH.sub.3 ; or PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is hydrogen; PA1 unsubstituted or substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; unsubstituted or substituted (C.sub.3 -C.sub.4)alkenyl wherein the substituent can be from one to three of the same or different phenyl, alkyl, carbo(C.sub.1 -C.sub.4)alkoxy, bromo, chloro or fluoro groups; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl, or naphthyl, (C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, benzyloxy, methylenedioxy, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 X, Y and Z are independently O or S provided that both X and Y are not O at the same time except that, in the case that X and Y are both O and Z is S, then R.sup.1 is n--C.sub.3 H.sub.7 or s--C.sub.4 H.sub.9, R.sup.2 is s--C.sub.4 H.sub.9, R.sup.3 is H, and R.sup.4 is CH.sub.3. PA1 R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is hydrogen; PA1 unsubstituted or substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl lring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms. PA1 R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl; PA1 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl or benzyl; PA1 R.sup.3 is hydrogen, methyl, or trifluoromethyl; and PA1 R.sup.4 is methyl, ethyl, n--propyl, propenyl or unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups. PA1 R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl; PA1 R.sup.2 is n--propyl, 3-pentyl, or 1-methylpropyl; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is methyl, ethyl, or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, methoxy, trifluoromethyl, nitro, or cyano groups; PA1 X and Y are, independently, O or S; and PA1 Z is O. PA1 (H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); PA1 (H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(O)(S sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); and PA1 (H.sub.5 C.sub.2 O)P(S)(S sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CF.sub.3 --3)(CHO)). PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.2 is unsubstituted or substituted C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same of different alkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different phenylcarbonyl, carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, benzoyl, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, or alkylthio, or amino or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 unsubstituted or substituted (C.sub.3 -C.sub.6)alkenyl wherein the substituent can be from one to three of the same or different phenyl, carbo(C.sub.1 -C.sub.4)alkoxy, bromo, chloro or fluoro groups; PA1 unsubstituted or substituted phenyl, or naphthyl, (C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different alkyl, haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- and di--alkyamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; and X, Y and Z are each O. PA1 R.sup.1 is unsubstituted or substituted (C.sub.1 -C.sub.4)alkyl wherein the substituent can be from one to three of the same or different bromo, chloro or fluoro groups; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.2 is unsubstituted or substituted (C.sub.2 -C.sub.5)alkyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 unsubstituted or substituted phenyl wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkythio, cyano, nitro, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; or unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to three of the same or different alkyl, haloalkyl, halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups; wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is substituted (C.sub.1 -C.sub.7)alkyl wherein the substituent can be one to three of the same or different carbo(C.sub.1 -C.sub.4)alkoxy, halo, alkoxy, alkylthio, cyano, nitro, unsubstituted or substituted phenoxy or phenylthio wherein the substituent can be from one to three of the same or different alkyl, alkoxy, halo, cyano, nitro, alkylthio, amino, or mono-- or di--alkylamino, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 unsubstituted or substituted phenyl(C.sub.1 -C.sub.3)alkyl wherein the substitutent is on the phenyl ring and wherein the substituent can be from one to five of the same or different halo or from one to three of the same or different haloalkyl containing one to three of the same or different halo, alkoxy, alkylthio, cyano, nitro, amino, or mono-- or di--alkylamino groups, wherein the alkyl moiety is straight or branched chain and contains from one to three carbon atoms; PA1 R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl, or benzyl; PA1 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl, or benzyl; PA1 R.sup.3 is hydrogen; and PA1 R.sup.4 is unsubstituted or substituted benzyl wherein the substituent is on the phenyl ring and wherein the substituent can be from one to two of the same or different (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups. PA1 R.sup.1 is methyl, ethyl, or 2,2,2-trifluoroethyl; PA1 R.sup.2 is n--propyl, 3-pentyl, or 1-methylpropyl; PA1 R.sup.3 hydrogen; and PA1 R.sup.4 is unsubstituted or substituted benzyl wherein the substituent can be from one to two (C.sub.1 -C.sub.3)alkyl, fluoro, chloro, bromo, trifluoromethyl, nitro or cyano groups. PA1 N-methyl-N-hydrogenthiocarbonyl-O-ethyl-S-n-butyl phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-n-butyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-n-butyl phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(1-pentyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(1-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(3-methylbutyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2,2-dimethylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-methoxyethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(3-nitropropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-nitro propyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-cyanoethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-chloropropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-fluoroethyl)phosophoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthiomethyl phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-ethylthioethyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-ethylthiomethyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-[(1,1-dimethylethyl)thiomethyl]phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-bromoallyl)phosphoroamidothioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(3-butenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(2-butenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-hexenyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-propargyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-propargyl phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-phenyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-phenyl phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-trichlorophenyl phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(1-phenylethyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-ethyl S-(5-phenyl-1-pentyl)phosphoroamidodithioate PA1 N-methyl N-methylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-butylcarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-heptyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-heptyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-(3-methoxypropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-methoxylpropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-chloropropyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-(3-chloropropyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(2-fluoroethyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-(2-fluoroethyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(2-butenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-(2-butenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(5-hexenyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(5-hexenyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothiaote PA1 N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1 methylpropyl)phosphoroamidothioate PA1 N-[(2-carboethoxy)-1-propenyl]N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-[(2-carboethoxy)-1-propenyl]N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-hexyn-1-yl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(3-hexyn-1-yl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-phenyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-phenyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-p-chlorobenzyl N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-p-chlorobenzyl N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(5-phenyl-1-pentyl)N-hydrogencarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-(5-phenyl-1-pentyl)N-hydrogenthiocarbonyl O-ethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl-O-propyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-propyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-n-butyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-(2,2,2-trifluoroethyl)S-1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-allyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarobnyl O-allyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarobnyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-(3-butenyl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-propargyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-(3-hexyn-1-yl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-phenyl S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-pheny S-(1methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogencarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidodithioate PA1 N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl)S-(1-methylpropyl)phosphoroamidothioate PA1 N-methyl N-hydrogenthiocarbonyl O-(2-phenylethyl S-(1-methylpropyl)phosphoroamidodithioate PA1 S,S'-dibutyl N-hydrogenthiocarbonyl N-methyl phosphoroamidodithioate PA1 N-hydrogencarbonyl N,S-dimethyl S'-(1-methylpropyl)phosphoroamidotrithioate PA1 N-methylthiocarbonyl N,S,S'-tripropyl phosphoroamidodithioate PA1 S-ethyl N-heptyl S'-propyl N-trifluoromethylcarbonyl phosphoroamidotrithioate PA1 S-methyl S'-pentyl N-propyl N-propoxymethylthiocarbonyl phosphoroamidodithioate PA1 S-ethyl S'-(2-hexenyl)N-methyl N-trifluoromethylthiocarbonyl phosphoroamidotrithioate PA1 N-ethyl S-methyl S'-(2-propenyl)N-trifluoromethyl phosphoroamidotrithioate PA1 N-ethyl N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate PA1 N-ethyl N-hydrogenthiocarbonyl S-(1-methylpropyl)S'-(2-propynyl)phosphoroamidotrithioate PA1 N-ethyl S-(2-hexynyl)N-hydrogencarbonyl S'-(1-methylpropyl)phosphoroamidotrithioate PA1 S-(2-fluorobutyl)N-hydrogenthiocarbonyl N-methyl S'-(1-methylethyl)phosphoroamidodithioate PA1 N-methylcarbonyl S-phenyl N,S'-dipropyl phosphoroamidodtrithioate PA1 S-benzyl S'-(1-ethylpropyl)N-hydrogenthiocarbonyl N-methyl phosphorotriamidothiate PA1 S-butyl N-ethyl N-methylcarbonyl S'-(5-phenylpentyl)phosphoroamidotrithioate PA1 S-butyl N-methylthiocarbonyl N-(2-propenyl)S'-propyl phosphoroamidodithioate PA1 N-(3-hexenyl)N-hydrogencarbonyl S,S'-dipropyl phosphoroamidotrithioate PA1 N-(3-hexynyl)N-hydrogenthiocarbonyl S-methyl S'-(1-methylpropyl)phosphoroamidodithioate PA1 S-ethyl N,S'-di-(3-propynyl)N-trifluoromethylthiocarbonyl phosphoroamidodithioate PA1 N-benzyl N-hydrogenthiocarbonyl S,S'-dipropyl phosphoroamidotrithioate PA1 N-(carbomethoxymethyl)-N-hydrogencarbonyl O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA1 N-(carboethoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphor oamidodithioate PA1 N-(cyanomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidod ithioate PA1 N-(methoxymethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroami dothioate PA1 N-(methylthiomethyl)-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoro amidodithioate PA1 N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA1 N-butyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA1 N-4-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid odithioate PA1 N-3-methoxybenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroami dodithioate PA1 N-3-trifluoromethylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phos phoroamidodithioate PA1 N-4-chlorophenylthiomethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)pho sphoroamidodithioate PA1 N-3-phenyl-2-butenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroa midodithioate PA1 N-1-methylbenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid odithioate PA1 N-4-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA1 N-4-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA1 N-phenyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidodithioat e PA1 N-4-chlorophenoxymethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosph oroamidodithioate PA1 N-1-naphthylmethyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroam idodithioate PA1 N-2-bromobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidod ithioate PA1 N-2-chloro-6-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phos phoroamidodithioate PA1 N-4-methylthiobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoro amidodithioate PA1 N-benzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA1 N-2-chloro-6-fluorobenzyl-O-ethyl-S-(1-methylpropyl)phosphoroamidothioate PA1 N-3-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid othioate PA1 N-2-fluorobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamid othioate PA1 N-3-cyanobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1methylpropyl)phosphoroamidot hioate PA1 N-3-nitrobenzyl-N-hydrogencarbonyl-O-ethyl-S-(1-methylpropyl)phosphoroamido thioate PA1 R.sup.1 is methyl, ethyl, 2,2,2-trifluoroethyl, phenyl or benzyl; PA1 R.sup.2 is unsubstituted straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl or benzyl; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is methyl, ethyl, n--propyl, propenyl, or unsubstituted or substituted benzyl; and PA1 X, Y and Z are, independently, O or S. PA1 (H.sub.5 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(C.sub.2 H.sub.5)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); PA1 (H.sub.2 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHO)); PA1 (H.sub.2 C.sub.2 O)P(O)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHS)); PA1 (H.sub.5 C.sub.2 O)P(S) (S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(S)(S--n--C.sub.3 H.sub.7)(N(CH.sub.3)(CHS)) PA1 (H.sub.5 C.sub.2 O)P(O)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHS)) PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 CF.sub.3)(CHO)) PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 CH.dbd.CH.sub.2)(CHO)); and PA1 (H.sub.5 C.sub.2 O)P(O)(S--3--pentyl)(N(C.sub.2 H.sub.5)(CHS)). PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHO)); PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(C.sub.2 H.sub.5)(CHS)); and PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.3)(CHO)). PA1 R.sup.1 is methyl, ethyl, 2,2,2-trifluoromethyl, phenyl or benzyl; PA1 R.sup.2 is unsubsitutued straight or branched chain (C.sub.3 -C.sub.5)alkyl, phenyl, or benzyl; PA1 R.sup.3 is hydrogen; PA1 R.sup.4 is unsubstituted or substituted alkyl or unsubstituted or substituted benzyl; and PA1 X, Y, and Z are each O. PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CN--4)(CHO)) PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9 )(N(CH.sub.2 C.sub.6 H.sub.4 F--4)(CHO)) PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 CN--4)(CHO)) PA1 (H.sub.5 C.sub.2 O)P(S)(S--sec--C.sub.4 H.sub.9)(N(CH.sub.2 C.sub.6 H.sub.4 NO.sub.2 --4)(CHO))
The several Magee patents, U.S. Pat. Nos. 3,716,600, 4,049,679 (and continuation-in-part thereof, 4,110,443), 3,914,417, 3,845,172, 3,885,032, and 3,825,634, disclose insecticidal phosphoroamidothioates and phosphoroamidodithioates and methods of killing insects therewith. Column 18, lines 1-8 of U.S. Pat. No. 3,716,600 discloses broadly that, in addition to foliar application of the insecticidal compounds, one or more of the compounds may be applied in other liquid or solid formulations to the insects, their environment or hosts, for example, directly to plants or soil so as to effect control of insects coming into contact therewith. The compounds have the formula EQU (RY)(R.sup.1 S)P(.dbd.O)(N(R.sup.3)(C(.dbd.O)R.sup.2)
wherein R, R.sup.1, R.sup.2, and R.sup.3, respectively, broadly, are alkyl, alkenyl, alkynyl, and haloalkyl, and Y is O or S.
The abstract of Japanese Pat. No. 77012251 discloses N--acyl--O--alkyl--S--alkyl(alkoxy, alkylthio, alkenyl, phenyl, alkoxycarbonyl, cyano, carbamoyl)--phosphoroamidothioates having insecticidal activity and having the formula EQU [(R.sup.2 C(O)--N(H)]P(.dbd.O)(OR.sup.1)(S(CH.sub.2).sub.n R.sup.3).
Osborne, U.S. Pat. No. 3,399,213, discloses parasiticidal and fungicidal acylphosphoroamidate compounds having the formulas EQU (G)(G)P(.dbd.Z)[N(G"')--C(.dbd.O)--G"--C(.dbd.O)-[OG']
and EQU (G)(G)P(50 Z)[N(O)--C(.dbd.O)--G"--O]
wherein G represents lower alkylamino, alkoxy, alkylthio, alkylphenyl, phenoxy, and substituted phenyl.
Braxton, Jr., et. al., U.S. Pat. No. 3,511,635, discloses herbicidal organophosphorous--nitrogen compounds having the formula EQU (R.sup.1)P(.dbd.X.sup.1)(--XR.sup.2)(.dbd.N(CH.sub.2).sub.n)
wherein
Kishino et. al., U.S. Pat. No. 3,760,043, disclose O--phenyl--S--alkyl--N--alkyl--phosphoroamidothioates which possess fungicidal, acaricidal, insecticidal, and nematocidal properties and have the formula EQU Aryl--O--P(.dbd.O)(NHR.sup.1)(SR.sup.2).
Schroeder, U.S. Pat. No. 3,657,426, discloses a method of controlling nematodes and other parasitic worm life existing in the soil at some stage of its life cycle by applying to the pests to be controlled or to the soil in which they live an effective amount of an O,O--dialkyl O-(1,2-dihydro-2-keto-1,6-dialkyl-4-pyridyl)phosphorothionate having the formula ##STR1##
Although the prior art discloses phosphoroamidothioate and phosphoroamidodithioate compounds having pesticidal, including insecticidal, activity, there remains a need for pesticidal compounds having improved pesticidal efficacy, and diminished detrimental effects such as mammalian toxicity and environmental waste, especially against soil insects such as the corn rootworm.
The prior art, including the several Magee patents described above which constitute the closest art known, do not provide any specific teaching illustrative of the insecticidal activity of the compounds therein disclosed when applied in the soil to protect against soil organisms. It is well known to those skilled in the art that organophosphates having a high order of contact insecticidal efficacy when applied to aerial, or foliar, portions of plants offer relatively little economic value as plant protectants when applied, or introduced, into the soil environment of the plants. Organophosphates tend to be susceptible to rapid degradative processes in the soil due to the combination of such factors as the hydrolytic action of soil moisture, unfavorable soil pH conditions, both of the above being exacerbated by the presence of soil microflora and fauna capable of rendering the insecticidal compound inactive. Application of a pesticide to the soil in ordinary agricultural practice does not necessarily or usually coincide with the presence of susceptible life stages of the target pest. For example, the hatching of insect eggs may be either delayed or it may occur over an interval of several days to several or many weeks. Insect ova are not generally affected by organophosphate pesticides. Thus, pesticidal compounds having satisfactory residual activity, especially in the soil--pesticidal compounds that retain their pesticidal efficacy under atmosphere conditions over an interval of several days to several or many weeks--are required in order to assure satisfactory protection of plants against soil insects. Further, it is highly desirable that such pesticidal compounds having activity persistent over an interval of several days to several or many weeks elicit control over a diverse selection of soil organisms that are agricultural pests.